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Harlingen

$145+ Cheap flights from Chicago (CHI) to Harlingen, TX (HRL)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HRL
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap flight deals from Chicago to Harlingen

Cheapest flights from Chicago to Harlingen
Explore the most affordable flight options available from Chicago to Harlingen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.

This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/303:50 pm
ORD
-
HRL
1 stop6h 20m
Southwest
Tue 4/77:10 am
HRL
-
ORD
1 stop6h 05m
Southwest
Deal found 2/2$211
This American Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:40 pm
ORD
-
HRL
1 stop6h 11m
American Airlines
Sat 4/112:47 pm
HRL
-
ORD
1 stop7h 58m
American Airlines
Deal found 2/1$273
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:25 am
ORD
-
HRL
1 stop8h 40m
Delta
Mon 4/204:02 pm
HRL
-
ORD
1 stop5h 36m
Delta
Deal found 2/2$279
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/44:03 pm
ORD
-
HRL
1 stop5h 56m
United Airlines
Tue 4/75:18 pm
HRL
-
ORD
1 stop7h 27m
United Airlines
Deal found 2/2$291
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/162:40 pm
ORD
-
HRL
2 stops9h 25m
Southwest
Thu 3/196:50 am
HRL
-
ORD
1 stop7h 30m
Southwest
Deal found 2/1$295
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/205:00 am
ORD
-
HRL
1 stop5h 12m
American Airlines
Fri 2/278:06 pm
HRL
-
ORD
1 stop4h 49m
American Airlines
Deal found 2/2$299
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/1610:49 am
ORD
-
HRL
1 stop7h 27m
American Airlines
Thu 2/198:06 pm
HRL
-
ORD
1 stop4h 49m
American Airlines
Deal found 2/2$309
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:48 am
ORD
-
HRL
1 stop5h 35m
United Airlines
Wed 4/155:18 pm
HRL
-
ORD
1 stop5h 57m
United Airlines
Deal found 2/2$330
This American Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/165:00 am
ORD
-
HRL
1 stop5h 12m
American Airlines
Fri 2/208:06 pm
HRL
-
ORD
1 stop4h 49m
American Airlines
Deal found 2/1$334
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:03 pm
ORD
-
HRL
1 stop5h 56m
United Airlines
Sat 4/117:00 am
HRL
-
ORD
2 stops13h 23m
United Airlines
Deal found 2/1$340
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/172:10 pm
ORD
-
HRL
1 stop7h 46m
United Airlines
Wed 3/1812:10 pm
HRL
-
ORD
1 stop7h 50m
United Airlines
Deal found 2/1$348

Find flight deals from Chicago to Harlingen

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Harlingen (HRL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$211
(Southwest)

One-way from

$145
(American Airlines)

Popular in

August

Cheapest in

April

Average price

$331
Provider with most accurate pricing for Chicago (CHI)-Harlingen Valley Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Harlingen Valley Intl flights.
Search Deals
From Chicago (CHI) to Harlingen Valley Intl
Search Deals
One-way flight from Chicago (CHI) to Harlingen Valley Intl
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($80 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Harlingen that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 3, 2026.
Use the filters below to find and compare flights from Chicago to Harlingen that are best for you.

Fly from

Chicago

Fly to

Harlingen

Route

Depart

Return

Price

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Fri 4/17

6:25 am-3:05 pm

1 stop8h 40m

Harlingen Valley Intl

Mon 4/20

4:02 pm-9:38 pm

1 stop5h 36m

$279

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Wed 4/15

5:48 am-11:23 am

1 stop5h 35m

Harlingen Valley Intl

Sat 4/18

5:18 pm-11:15 pm

1 stop5h 57m

$291

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Sat 4/25

10:35 am-4:04 pm

1 stop5h 29m

Harlingen Valley Intl

Tue 4/28

5:18 pm-11:15 pm

1 stop5h 57m

$291

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Wed 4/22

5:48 am-11:23 am

1 stop5h 35m

Harlingen Valley Intl

Sat 4/25

7:00 am-12:57 pm

1 stop5h 57m

$291

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Sat 4/11

2:05 pm-7:40 pm

1 stop5h 35m

Harlingen Valley Intl

Tue 4/14

5:18 pm-11:15 pm

1 stop5h 57m

$291

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Sat 4/4

4:03 pm-9:59 pm

1 stop5h 56m

Harlingen Valley Intl

Tue 4/7

5:18 pm-12:45 am

1 stop7h 27m

$291

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Mon 3/30

4:15 pm-12:05 am

2 stops7h 50m

Harlingen Valley Intl

Tue 4/7

7:10 am-1:15 pm

1 stop6h 05m

$295

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Fri 2/20

5:00 am-10:12 am

1 stop5h 12m

Harlingen Valley Intl

Fri 2/27

8:06 pm-12:55 am

1 stop4h 49m

$299

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Mon 2/16

10:49 am-6:16 pm

1 stop7h 27m

Harlingen Valley Intl

Thu 2/19

8:06 pm-12:55 am

1 stop4h 49m

$309

ChicagoHarlingen

ORD - HRL

ORDHRL

Chicago O'Hare Intl

Tue 2/17

2:00 pm-9:59 pm

1 stop7h 59m

Harlingen Valley Intl

Sat 2/21

5:22 pm-12:26 am

1 stop7h 04m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 20 results
1
2

Compare providers for flights from Chicago to Harlingen

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Harlingen in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Harlingen, Texas flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Harlingen, Texas flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Harlingen, Texas flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Harlingen, Texas flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Harlingen, Texas flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Harlingen

Have a flexible travel schedule? Discover the best time to fly to Harlingen from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Harlingen

What is the cheapest month to book a flight from Chicago to Harlingen, Texas?

Currently, November is the cheapest month in which you can book a flight from Chicago to Harlingen, Texas (average of $185). Flying from Chicago to Harlingen, Texas in December is currently the most expensive (average of $277). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Chicago to Harlingen, Texas?

What’s the top layover airport for flights from Chicago to Harlingen, Texas?

Share of 1-stop round-trip flights from Chicago to Harlingen, Texas chosen by Cheapflights users in the past 12 months, using the same layover each way.

Austin (AUS) – chosen by Cheapflights users on 92% of 1-stop itineraries from Chicago to Harlingen, Texas on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Harlingen, Texas?

Average round-trip fare for 1-stop flights from Chicago to Harlingen, Texas, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Austin (AUS) is the most affordable 1-stop option, with an average round-trip price of $261.

What’s the fastest layover option from Chicago to Harlingen, Texas?

Shortest average travel time for 1-stop one-way flights from Chicago to Harlingen, Texas, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Houston (IAH) have the shortest average one-way travel time for 1-stop routes: 5h 19m.

Which airport typically offers the quickest layover for flights from Chicago to Harlingen, Texas?

Average layover duration for 1-stop one-way flights from Chicago to Harlingen, Texas, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Houston (IAH) offer the fastest connection on this route, with an average layover time of 1h 30m.

Reviews of airlines servicing Harlingen

Get insights into the airlines that provide service to Harlingen. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Harlingen. Reviews last updated February 3, 2026.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Harlingen to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,272 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,236 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,217 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Harlingen. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Harlingen from Chicago?

    Located just 3.7 mi from the city center, Harlingen Valley Intl is the airport most travelers will use when flying to Harlingen from Chicago. Booking flights from Chicago to Valley Intl (HRL) should be relatively easy as there are 0 daily inbound flights from Chicago from 3 different airlines.

  • How long is the flight from Chicago to Harlingen, Texas?

    There are many flights that can get you from Chicago to Harlingen, Texas in 5h 35m. Fly via Delta or United Airlines to get the fastest option. Chicago and Harlingen, Texas are separated by a distance of 1220 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Harlingen, Texas round-trip?

    According to our current data, Southwest ($222), United Airlines ($251), and American Airlines ($278) offers the cheapest pricing from Chicago to Harlingen, Texas. Users have found that Southwest is 37% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago to Harlingen, Texas one-way?

    The cheapest airlines for a one-way flight from Chicago to Harlingen, Texas are American Airlines ($108), United Airlines ($108), and Southwest ($118).

  • Can I find deals for flights from Chicago to Harlingen that include hotel bookings?

    Yes. In addition to deals on Chicago to Harlingen flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Harlingen?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Harlingen.

  • Can I find deals for business class flights from Chicago to Harlingen?

    Yes. Cheapflights offers flight deals from Chicago to Harlingen by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Harlingen, Texas?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Harlingen, Texas (average of $185). Flying from Chicago to Harlingen, Texas in December is currently the most expensive (average of $277). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Harlingen

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Harlingen

Discover the top 3 airlines that operate flights from Chicago to Harlingen. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$222Average$345FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$251Average$359FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$278Average$348FlexibilityNo cancel feeOn-time71%

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